Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device

ABSTRACT

Disclosed is a light-emitting material for organic electroluminescent (EL) devices which is composed of an asymmetric anthracene derivative of a specific structure. Also disclosed are a material for organic EL devices and an organic EL device wherein an organic thin film layer composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode. At least one layer composed of the organic thin film layer contains the material for organic EL devices by itself or as a component of a mixture. Consequently, the organic EL device has a high efficiency and a long life. Also disclosed are a light-emitting material for organic EL devices and material for organic devices which enable to realize such an organic EL device.

TECHNICAL FIELD

The present invention relates to a light emitting material for anorganic electroluminescence device, an organic electroluminescent deviceusing the material and a material for an organic electroluminescentdevice, in particular, to an organic electroluminescence deviceexhibiting high current efficiency and having a long lifetime, and alsoto a light-emitting material for an organic electroluminescence deviceand a material for an organic electroluminescent device for realizingthe organic EL device.

BACKGROUND ART

An organic electroluminescence (“electroluminescence” will beoccasionally referred to as “EL”, hereinafter) device is a spontaneouslight emitting device which utilizes the principle that a fluorescentsubstance emits light by energy of recombination of holes injected froman anode and electrons injected from a cathode when an electric field isapplied. Since an organic EL device of the laminate type driven under alow electric voltage was reported by C. W. Tang et al. of Eastman KodakCompany (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Volume51, Pages 913, 1987), many studies have been conducted on organic ELdevices using organic materials as the constituting materials.

Tang et al. used a laminate structure using tris(8-hydroxyquinolinolaluminum) for the light emitting layer and a triphenyldiamine derivativefor the hole transporting layer. Advantages of the laminate structureare that the efficiency of hole injection into the light emitting layercan be increased, that the efficiency of forming excited particles whichare formed by blocking and recombining electrons injected from thecathode can be increased, and that excited particles formed among thelight emitting layer can be enclosed

As the structure of the organic EL device, a two-layered structurehaving a hole transporting (injecting) layer and an electrontransporting and light emitting layer and a three-layered structurehaving a hole transporting (injecting) layer, a light emitting layer andan electron transporting (injecting) layer are well known. To increasethe efficiency of recombination of injected holes and electrons in thedevices of the laminate type, the structure of the device and theprocess for forming the device have been studied. As the light emittingmaterial of the organic EL device, chelate complexes such astris(8-quinolinolato)aluminum, coumarine derivatives,tetraphenylbutadiene derivatives, bisstyrylarylene derivatives andoxadiazole derivatives are known. It is reported that light in thevisible region ranging from blue light to red light can be obtained byusing these light emitting materials, and development of a deviceexhibiting color images is expected (refer to, for example, Patentliteratures 1, 2 and 3).

In addition, Patent literature 4 discloses a device havingphenylanthracene derivatives as a light emitting material. Although theanthracene derivatives were used as a blue light emitting material, ithas been required to extend a lifetime of the device. A material havingnaphthyl groups at 9th and 10th positions of anthracene is disclosed inPatent literature 5 and a material having fluoranthene at 9th and 10thpositions for a device is disclosed in Patent literature 6. Althoughthese anthracene derivatives were used as a blue light emittingmaterial, it has been required to improve a lifetime of the device.

Further, Patent literature 7 discloses various types of anthracenederivatives to be used for a hole transporting material. However, thesehave not yet been evaluated as a light emitting material.

-   [Patent literature 1] Japanese Patent Application Laid-Open No.    Heisei 8(1996)-239655-   [Patent literature 2] Japanese Patent Application Laid-Open No.    Heisei 7(1995)-138561-   [Patent literature 3] Japanese Patent Application Laid-Open No.    Heisei 3(1991)-200289-   [Patent literature 4] Japanese Patent Application Laid-Open No.    Heisei 8(1996)-012600-   [Patent literature 5] Japanese Patent Application Laid-Open No.    Heisei 11(1999)-3782-   [Patent literature 6] Japanese Patent Application Laid-Open No.    2001-257074-   [Patent literature 7] Japanese Patent Application Laid-Open No.    2000-182776

DISCLOSURE OF THE INVENTION

The present invention has been made to overcome the above problems andhas an objective of providing an organic electroluminescence deviceexhibiting a great efficiency of light emission and having a longlifetime, and also to a light emitting material for realizing theorganic EL device and a material for an organic electroluminescentdevice for realizing the organic EL device.

As a result of intensive researches and studies to achieve the aboveobjective by the present inventors, it was found that employing acompound having a specific asymmetric anthracene structure representedby the following general formula (1) as a light emitting material of anorganic EL device enables to provide the organic EL device exhibiting agreat efficiency of light emission and having a long lifetime.

In other word, the present invention provides a martial for an organicEL device comprising an asymmetric anthracene derivative represented bythe following general formula (1), and an organic EL device comprisingat least one of organic thin film layers including a light emittinglayer interposed between a pair of electrode consisting of an anode anda cathode, wherein the organic thin film layer contains at least oneselected from the aforementioned asymmetric anthracene derivativesrepresented the general formula (1) singly or as a component of mixturethereof.

In the general formula (1), A¹ and A² each independently represents asubstituted or unsubstituted condensed aromatic hydrocarbon ring grouphaving ring carbon atoms of 10 to 20. Ar¹ and Ar² each independentlyrepresents a hydrogen atom, a substituted or unsubstituted aromatichydrocarbon ring group having ring carbon atoms of 6 to 20. R¹ to R⁸each independently represents a hydrogen atom, a substituted orunsubstituted aromatic hydrocarbon ring group having ring carbon atomsof 6 to 50, a substituted or unsubstituted aromatic hetero ring grouphaving ring atoms of 5 to 50, a substituted or unsubstituted alkyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstitutedcycloalkyl group having carbon atoms of 3 to 50, a substituted orunsubstituted alkoxy group having carbon atoms of 1 to 50, a substitutedor unsubstituted aralkyl group having carbon atoms of 6 to 50, asubstituted or unsubstituted aryloxy group having carbon atoms of 5 to50, a substituted or unsubstituted arylthio group having carbon atoms of5 to 50, a substituted or unsubstituted alkoxycarbonyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted silyl group, acaboxyl group, a halogen atom, a cyano group, a nitro group or ahydroxyl group. R⁹ to R¹⁰ each independently represents a hydrogen atom,a substituted or unsubstituted aromatic hydrocarbon ring group havingring carbon atoms of 6 to 50, a substituted or unsubstituted alkyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstitutedcycloalkyl group having carbon atoms of 3 to 50, a substituted orunsubstituted alkoxy group having carbon atoms of 1 to 50, a substitutedor unsubstituted aralkyl group having carbon atoms of 6 to 50, asubstituted or unsubstituted aryloxy group having carbon atoms of 5 to50, a substituted or unsubstituted arylthio group having carbon atoms of5 to 50, a substituted or unsubstituted alkoxycarbonyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted silyl group, acaboxyl group, a halogen atom, a cyano group, a nitro group or ahydroxyl group, and none of R⁹ and R¹⁰ is alkenyl group. Ar¹, Ar², R⁹and R¹⁰ each may be a plural number, and two neighboring groups thereofmay form a saturated or unsaturated ring structure; however, it isexcluded a case where the groups at 9th and 10th positions of anthraceneat the core in the general formula (1) are symmetrical at x-y axis ofsymmetry and bond each other.

In addition, the present invention provides a material for an organic ELdevice comprising an asymmetric anthracene derivative represented by thefollowing general formula (1′).

A material for an organic electroluminescent device comprising anasymmetric derivative represented by the following general formula (1′).

In the general formula (1′), A^(1′) and A^(2′) each independentlyrepresents a substituted or unsubstituted condensed aromatic hydrocarbonring group having ring carbon atoms of 10 to 20, and at least one ofA^(1′) and A^(2′) represents a naphtalene-1-yl group having asubstituent at 4th position thereof or a substituted or unsubstitutedcondensed aromatic hydrocarbon ring group having ring carbon atoms of 12to 20. Ar¹, Ar² and R¹ to R¹⁰ each independently represent the same withthe aforementioned; however, in the general formula (1′), it is excludeda case where the groups at 9th and 10th positions of anthracene at thecore are symmetrical at x-y axis of symmetry and bond each other.

The light emitting material for an organic EL device or the organic ELdevice employed the asymmetric anthracene derivatives of the presentinvention exhibits high current efficiency and has a long lifetime.

INDUSTRIAL APPLICABILITY

As explained above in details, the light emitting material for anorganic EL device or the organic EL device employed the asymmetricanthracene derivatives of the present invention represented by thegeneral formula (1) exhibits high current efficiency and has a longlifetime. Therefore, the organic EL device is valuable for potentialcontinuous use for a prolonged period.

THE PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The light emitting material for an organic EL device comprises theasymmetric anthracene derivative represented by the general formula (1).It is excluded a case where the groups at 9th and 10th positions ofanthracene at the core are symmetrical at x-y axis of symmetry and bondeach other in the asymmetric derivatives represented by the generalformula (1), which means that the general formula (1) is preferably thefollowing structures:

-   (I) A¹ is different from A².-   (II) when A¹ is the same with A², (II-i) Ar¹ is different from Ar²,    or (II-ii) R⁹ is different from R¹⁰, and-   (II-iii) when Ar¹ and Ar² are the same with each other, and R⁹ and    R¹⁰ are the same with each other,-   (II-iii-1) the bonding position of A¹ to 9th position of the    anthracene ring is different from the bonding position of A² to 10th    position of the anthracene ring,-   (II-iii-2) when both Ar¹ and Ar² are not hydrogen atoms, the bonding    position of Ar¹ to A¹ is different from the bonding position of Ar²    to A², and-   (II-iii-3) when both R⁹ and R² are not hydrogen atoms, the bonding    position of R⁹ to A¹ different from the bonding position of R¹⁰ to    A².

In the general formula (1), A¹ and A² each independently is asubstituted or unsubstituted condensed aromatic hydrocarbon ring havingring carbon atoms of 10 to 20, preferably 10 to 16.

Examples of the substituted or unsubstituted condensed aromatichydrocarbon ring group represented by Ar¹ and Ar² include 1-naphthylgroup, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthrylgroup, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthylgroup, 4-methyl-1-anthryl group and the like. Among those, 1-naphthylgroup, 2-naphthyl group and 9-phenanthryl group are preferred. In thegeneral formula (1), Ar¹ and Ar² each independently represents ahydrogen atom or a substituted or unsubstituted aromatic hydrocarbonring having ring carbon atoms of 6 to 50, preferably 6 to 16.

Examples of the substituted or unsubstituted aromatic hydrocarbon ringgroup represented by A¹ and A² include phenyl group, 1-naphthyl group,2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group,1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropy)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group, 4″-t-butyl-p-terphenyl-4-yl group andthe like.

Among those, phenyl group, 1-naphthyl group, 2-naphthyl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-tolylgroup, m-tolyl group, p-tolyl group, p-t-butylphenyl group arepreferred.

In the general formula (1), R¹ to R⁸ each independently represents ahydrogen atom, a substituted or unsubstituted aromatic hydrocarbon ringgroup having ring carbon atoms of 6 to 50, a substituted orunsubstituted aromatic hetero ring group having ring atoms of 5 to 50, asubstituted or unsubstituted alkyl group having carbon atoms of 1 to 50,a substituted or unsubstituted cycloalkyl group having carbon atoms of 3to 50, a substituted or unsubstituted alkoxy group having carbon atomsof 1 to 50, a substituted or unsubstituted aralkyl group having carbonatoms of 6 to 50, a substituted or unsubstituted aryloxy group havingcarbon atoms of 5 to 50, a substituted or unsubstituted arylthio grouphaving carbon atoms of 5 to 50, a substituted or unsubstitutedalkoxycarbonyl group having carbon atoms of 1 to 50, a substituted orunsubstituted silyl group, a caboxyl group, a halogen atom, a cyanogroup, a nitro group or a hydroxyl group.

R⁹ to R¹⁰ each independently represents a hydrogen atom, a substitutedor unsubstituted aromatic hydrocarbon ring group having ring carbonatoms of 6 to 50, a substituted or unsubstituted alkyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl grouphaving carbon atoms of 3 to 50, a substituted or unsubstituted alkoxygroup having carbon atoms of 1 to 50, a substituted or unsubstitutedaralkyl group having carbon atoms of 6 to 50, a substituted orunsubstituted aryloxy group having carbon atoms of 5 to 50, asubstituted or unsubstituted arylthio group having carbon atoms of 5 to50, a substituted or unsubstituted alkoxycarbonyl group having carbonatoms of 1 to 50, a substituted or unsubstituted silyl group, a caboxylgroup, a halogen atom, a cyano group, a nitro group or a hydroxyl group,and none of R⁹ and R¹⁰ is alkenyl group. Examples of a substituted orunsubstituted aromatic hydrocarbon ring group represented by R¹ to R¹⁰include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthrylgroup, 2-anthryl group, 9-anthryl group, 1-phenanthryl group,2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group,9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group,9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4′-methylbiphenylylgroup, 4″-t-butyl-p-terphenyl-4-yl group and the like.

Examples of a substituted or unsubstituted aromatic hetero ring grouprepresented by R¹ to R⁸ include 1-pyrrolyl group, 2-pyrrolyl group,3-pyrrolyl group, pyradinyl group, 2-pyridinyl group, 3-pyridinyl group,4-pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group,4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group,1-isoindolyl group, 2-isoindolyl group, 3-isoindolyl group, 4-isoindolylgroup, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group,2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranylgroup, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group,7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group,4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranylgroup, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group,4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group,8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group,4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group,7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group,5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolylgroup, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group,1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinylgroup, 4-phenanthridinyl group, 6-phenanthridinyl group,7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinylgroup, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group,3-acridinyl group, 4-acridinyl group, 9-acridinyl group,1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group,1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group,2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolylgroup, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group,3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group,2-methylpyrrol-4-yl group, 2-methylpyrrole-5-yl group,3-methylpyrrole-1-yl group, 3-methylpyrrole-2-yl group,3-methylpyrrole-4-yl group, 3-methylpyrrole-5-yl group,2-t-butylpyrrole-4-yl group, 3-(2-phenylpropyl)pyrrole-1-yl group,2-carbinyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolylgroup, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group,4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group,4-t-butyl-3-indolyl group and the like.

Examples of a substituted or unsubstituted alkyl group represented by R¹to R¹⁰ includes methyl group, ethyl group, propyl group, isopropylgroup, n-butyl group, s-butyl group, isobutyl group, t-butyl group,n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group,hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group,2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triamino-propyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyano-propyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and thelike.

Examples of s substituted or unsubstituted cycloalkyl group representedby R¹ to R¹⁰ include cyclopropyl group, cyclobutyl group, cyclopentylgroup, cyclohexyl group, 4-methylcyclohexyl group, 1-adamanthyl group,2-adamanthyl group, 1-norbornyl group, 2-norbornyl group and the like.

A substituted or unsubstituted alkoxy group represented by R¹ to R¹⁰ isrepresented by —OY and examples of Y include methyl group, ethyl group,propyl group, isopropyl group, n-butyl group, s-butyl group, isobutylgroup, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group,n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethylgroup, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triamino-propyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyano-propyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and thelike.

Examples of a substituted or unsubstituted aralkyl group represented byR¹ to R¹⁰ includes benzyl group, 1-phenylethyl group, 2-phenylethylgroup, 1-phenyl-isopropyl group, 2-phenylisopropyl group, phenyl-t-butylgroup, α-naphthylmethyl group, 1-α-naphthylethyl group,2-α-naphthylethyl group, 1-α-naphthylisopropyl group,2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethylgroup, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group,2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethylgroup, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group,p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group,p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group,p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group,p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group,p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group,p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group,p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group,1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group andthe like. A substituted or unsubstituted aryloxy group represented by R¹to R¹⁰ is represented by —OY′, and examples of Y′ include phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group,9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthrylgroup, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenyl-yl group, 4″-t-butyl-p-terphenyl-4-yl group,2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group,3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group,3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group,7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolylgroup, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group,2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranylgroup, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group,7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group,4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranylgroup, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group,4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group,8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group,4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group,7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group,5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolylgroup, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group,2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinylgroup, 6-phenanthridinyl group, 7-phenanthridinyl group,8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinylgroup, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group,4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group,1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group,1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group,1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group,1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group,1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group,1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group,1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group,1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group,1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group,1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group,1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group,1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group,1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group,1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group,2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group,2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group,2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group,2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group,2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group,2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group,2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group,2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group,2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group,2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group,2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group,2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group,1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group,4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolylgroup, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group,3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-ylgroup, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methylpyrrole-5-yl group, 3-methylpyrrole-1-yl group,3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group,3-methylpyrrole-5-yl group, 2-t-butylpyrrole-4-yl group,3-(2-phenylpropyl)pyrrole-1-yl group, 2-methyl-1-indolyl group,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group, 4-t-butyl-3-indolyl group and the like.

A substituted or unsubstituted arylthio group represented by R¹ to R¹⁰is represented by —SY″, and examples of Y″ include phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group,9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthrylgroup, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenyl-yl group, 4″-t-butyl-p-terphenyl-4-yl group,2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group,3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group,3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group,7-indolyl group, 1-isoindolyl group, 3-isoindolyl group, 4-isoindolylgroup, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group,2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranylgroup, 4-benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group,7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group,4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranylgroup, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group,4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group,8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group,4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group,7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxanyl group,5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolyl group, 2-carbazolylgroup, 3-carbazolyl group, 4-carbazolyl group, 1-phenanthridinyl group,2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinylgroup, 6-phenanthridinyl group, 7-phenanthridinyl group,8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinylgroup, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group,4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group,1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group,1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group,1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group,1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group,1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group,1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group,1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group,1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group,1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group,1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group,1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group,1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group,1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group,1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group,2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group,2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group,2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group,2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group,2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group,2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group,2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group,2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group,2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group,2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group,2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group,2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group,1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group,4-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolylgroup, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group,3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-ylgroup, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methylpyrrole-5-yl group, 3-methylpyrrole-1-yl group,3-methylpyrrole-2-yl group, 3-methylpyrrole-4-yl group,3-methylpyrrole-5-yl group, 2-t-butylpyrrole-4-yl group,3-(2-phenylpropyl)pyrrole-1-yl group, 2-methyl-1-indolyl group,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl 1-indolyl group, 4-t-butyl 1-indolyl group, 2-t-butyl3-indolyl group, 4-t-butyl 3-indolyl group and the like.

A substituted or unsubstituted alkoxycarbonyl group for R¹ to R¹⁰ isrepresented by —COOZ, and examples of Z include methyl group, ethylgroup, propyl group, isopropyl group, n-butyl group, s-butyl group,isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptylgroup, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group,2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triamino-propyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyano-propyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group and thelike.

Examples of a halogen atom for R¹ to R¹⁰ fluorine atom, chlorine atom,bromine atom and the like

A substituent for the Ar¹, Ar² and R¹ to R¹⁰ includes halogen atom,hydroxyl group, nitro group, cyano group, alkyl group, aryl group,cycloalkyl group, alkoxy group, aralkyl group, aryloxy group, arylthiogroup, alkoxycarbonyl group, carboxyl group or the like.

Ar¹, Ar², R⁹ and R¹⁰ each may be a plural number, and two neighboringgroups thereof may form a saturated or unsaturated ring structure, andthe ring structure includes, in addition to unsaturated 6 member ringsuch as benzene, saturated or unsaturated 5 member or 7 member ringstructure and the like.

Further, in the present invention, it is preferable that the asymmetricanthracene derivatives represented by the aforementioned general formula(1) comprise a naphthalene-1-yl group having substituent at 4th positionthereof and/or a substituted or unsubstituted condensed aromatichydrocarbon ring having ring carbon atoms of 12 to 20. Examples of thesubstituent includes the same with the substituent of the groupsrepresented by Ar¹, Ar² and R¹ to R¹⁰

The material for the organic EL device of the present inventioncomprises the asymmetric anthracene derivatives represented by theaforementioned general formula (1′). The general formula (1′) is shownby that A^(1′) and A^(2′) each independently are limited to asubstituted or unsubstituted condensed aromatic hydrocarbon ring havingring carbon atoms of 10 to 20, and at least one of A^(1′) and A^(2′) islimited to naphthalene-1-yl group having substituent at 4th positionthereof or a substituted or unsubstituted condensed aromatic hydrocarbonring having ring carbon atoms of 12 to 20. Ar¹, Ar² and R¹ to R¹⁰ eachindependently is the same with aforementioned so that examples of eachgroup thereof and preferable groups, and examples of the substituent arethe same with aforementioned.

In addition, as mentioned in the general formula (1), it is excluded acase where the groups at 9th and 10th positions of anthracene at thecore in the general formula (1′) are symmetrical at x-y axis of symmetryand bond each other. As the general formula (1) includes the generalformula (1′), the general formula (1′) is included in the generalformula (1) when it is called simply “the general formula (1)”.

Specific examples of the asymmetric anthracene of the present inventionrepresented by the general formula (1) include as follows, but notlimited thereto:

The asymmetric anthracene derivatives represented by the general formula(1) may be synthesized by using an aryl halide compound and ananthracene boronic acid compound as starting materials and applyingappropriate combination of Suzuki-coupling reaction, halogenationreaction and esterification by boric acid through known methods. Thefollowing is a synthesis scheme:

Many reports have been made on the Suzuki-coupling reaction (Chem. Rev.,Vol. 95, No. 7, 2457 (1995), etc.) and the reaction conditions describedin the reports may be applied. The reaction may be carried out at normalpressure or as appropriate, under pressure in inert gas atmosphere suchas nitrogen, argon and helium. The reaction temperature is in the rangefrom 15 to 300 deg C., preferably 30 to 200 deg C. The reaction solventincludes water, aromatic hydrocarbon such as benzene, toluene andxylene, ether such as 1,2-dimethoxyethane, diethylether,methyl-t-butylether, tetrahydrofuran and dioxane, saturated hydrocarbonsuch as pentane, hexane, heptane, octane and cyclohexane, halide such asdichloromethane, chloroform, tetrachloromethane, 1,2-dichloroethane and1,1,1-trichloroethane, nitrile such as acetonitrile and benzonitrile,ester such as ethylacetate, methylacetate and butylacetate, and amidesuch as N,N-dimethylformamide, N,N-dimethylacetoamide andN-merthypyrrolidone. These solvent may used singly or as a component ofmixture thereof. Among those, toluene, 1,2-dimethoxyethane, dioxane andwater are preferred. Amount of the solvent to be used is generally 3 to50 fold by weight, preferably 4 to 20 fold by weight to aryl boronicacid or derivatives thereof.

The base to be used for the reaction includes, for example, sodiumcarbonate, potassium carbonate, sodium hydroxide, potassium hydroxide,sodium bicarbonate, potassium bicarbonate, magnesium carbonate, lithiumcarbonate, potassium fluoride, cesium fluoride, cesium chloride, cesiumbromide, cesium carbonate, potassium phosphate, sodium methoxide,potassium t-butoxide, sodium t-butoxide, lithium t-botoxide and thelike, and sodium carbonate is preferable. Amount of the base to be usedis generally 0.7 to 10 moles in equivalence, preferably 0.9 to 6 molesin equivalence to aryl boronic acid or derivatives thereof.

The catalysts to be used for the reaction include, for example,palladium catalysts such as tetrakis(triphenylphosphine)palladium,dichlorobis(triphenylphosphine)palladium,dichloro[bis(diphenylphosphono)ethane]palladium,dichloro[bis(diphenylphosphono)propane]palladium,dichloro[bis(diphenylphosphono)butane]palladium,dichloro[bis(diphenylphosphono)ferrocene]palladium and the like, nickelcatalysts such as tetrakis(triphenylphosphine)nickel,dichlorobis(triphenylphosphine)nickel,dichloro[bis(diphenylphosphono)ethane]nickel,dichloro[bis(diphenylphosphono)propane]nickel,dichloro[bis(diphenylphosphono)butane]nickel,dichloro[bis(diphenylphosphono)ferrocene]nickel and the like, andtetrakis(triphenylphosphine)palladium is preferable.

Amount of the catalyst to be used is generally 0.001 to 1 mole inequivalence, preferably 0.01 to 0.1 mole in equivalence to an arylhalide compound.

Halogen for the aryl halide compounds includes, for example, an iodineatom, a bromine atom, a chlorine atom and the like, and a iodine atomand a bromine atom are preferable. Although a halogenations agent forthe halogenations reaction is not limited, for example, N-halogenatedchlorosuccinimide is preferably used. Amount of the halogenations agentto be used is generally 0.8 to 10 moles in equivalence, preferably 1 to5 moles in equivalence to an aryl compound. The reaction is generallycarried out in an inert solvent under inert atmosphere such as nitrogen,argon, helium and the like.

The inert solvent to be used includes, for example,N,N-dimethylformamide, N,N-dimethylacetoamide, N-methylpyrrolidone,dimethylsulfoxide, carbon tetrachloride, chlorobenzene, dichlorobenzene,nitrobenzene, toluene, xylene, methylcellosolve, ethylcellosolve, waterand the like, and N,N-dimethylformamide and N-methylpyrrolidone arepreferable. Amount of the solvent to be used is generally 3 to 50 foldby weight, preferably 5 to 20 fold by weight to an aryl compound. Thereaction temperature is generally in the range from 0 to 200 deg C.,preferably 20 to 120 deg C.

The esterification by boric acid may be carried out in accordance withknown methods (Japan Chemical Society's editorial, The ExperimentalChemistry Course No. 4 edition, Vol 24, 61-90; J. Org. Chem., Vol. 60,7508 (1995), etc.) For example, by way of lithiation or Grignardreaction of an arylhalide compound, the esterification by boric acid iscarried out generally under an inert atmosphere such as nitrogen, argon,helium and by using an inert solvent as a reaction solvent. The solventsinclude, for example, saturated hydrocarbon such as pentane, hexane,heptane, octane and cyclohexane, ether such as 1,2-dimethoxyethane,diethylether, methyl-t-butylether, tetrahydrofuran and dioxane, aromatichydrocarbon such as benzen, toluene and xylene. These may be used singlyor as mixture thereof, and dimethylether and toluene are preferred.

Amount of the solvent to be used is generally 3 to 50 fold by weight,preferably 4 to 20 fold by weight to an arylhalide compound.

The lithiation reagent to be used includes, for example, alkyl metalreagent suc as n-butyllithium, t-butyllithium, phenylithium andmethyllithium, amido-base such as lithium diisopropylamide andlithiumbistrimethylsilylamide, and n-butyllithium is preferred. Further,Grignard reagent may be prepared by reacting an arylhalide compound anda magnesium metal. Trialkyl borate to be used as esterification agent byboronic acid includes trimethyl borate, triethyl borate, triisopropylborate, triibutyl borate and the like, and trimethyl borate andtriisopropyl borate are preferred. Each amount of the lithiation reagentand a magnesium metal to be used is generally from 1 to 10 moles inequivalence, preferably from 1 to 2 moles in equivalence respectively toan arylhalide compound. Amount of trialkyl borate to be used isgenerally from 1 to 10 moles in equivalence, preferably from 1 to 5moles in equivalence to an arylhalide compound (or a pyrenylhalidecompound). The reaction temperature is in the range from −100 to 50° C.,preferably −75 to 10 deg C.

An organic EL device of the present invention which comprises at leastone organic thin film layer, which contains at least a light emittinglayer, interposed between a pair of electrode consisting of an anode anda cathode, wherein the organic thin film layer comprises at least one,singly or as a component of a mixture thereof. It is preferable that theaforementioned light emitting layer comprises the aforementioned lightemitting material for the organic EL device or the aforementionedmaterial for the organic EL device singly or as a component of mixturethereof.

It is preferable that the aforementioned organic thin layer comprisesthe aforementioned light emitting material for the organic EL device orthe aforementioned material for the organic EL device as a hostmaterial. In addition, the organic EL device of the present invention ispreferred if the aforementioned light emitting layer contains further anarylamine compound and/or a styrylamine compound. The styrylaminecompounds are shown by the following general formula (A):

In the general formula above, Ar³ represents a group selected from aphenyl group, a biphenyl group, a terphenyl group, a stilbene group anda distyryl aryl group, and Ar⁴ and Ar⁵ each independently represents ahydrogen atom or an aromatic hydrocarbon ring group having 6 to 20 ringcarbon atoms. Ar³, Ar⁴ and Ar⁵ each may be substituted, p represents aninteger of 1 to 4, and more preferably, at least one of Ar⁴ and Ar⁵ issubstituted with a styryl group.

In the preceding description, the aromatic hydrocarbon ring group having6 to 20 carbon atoms includes preferably a phenyl group, a naphthylgroup, an anthranil group, a phenanthryl group, a terphenyl group andthe like. The preferred arylamine compounds are represented by thegeneral formula (B):

In the general formula above, Ar⁶ to Ar⁸ each independently represents asubstituted or unsubstituted aryl group having 5 to 40 ring carbonatoms. q represents an integer of 1 to 4.

In the preceding description, the aryl group having 5 to 40 ring carbonatoms include preferably a phenyl group, a naphthyl group, an anthranilgroup, a phenanthryl group, a pyrenyl group, a coronyl group, a biphenylgroup, a terphenyl group, a pyrrolyl group, a furanyl group, athiophenyl group, a benzthiophenyl group, an oxadiazolyl group, adiphenylanthranil group, an indolyl group, a carbazolyl group, a pyridylgroup, a benzoquinolyl group, a fluoranthenyl group, anacenaphthofluoranthenyl group, a stilbene group, a perylenyl group, achrysenyl group, a picenyl group, a triphenylenyl group, a runicenylgroup, a benzoanthracenyl group, a phenylanthranyl group, bisanthracenylgroup or an aryl group represented by the following general formulae (C)and (D), and the like:

In the general formula (C), n represents an integer of 1 to 3.Additionally, preferable examples of the substituent for aforementionedaryl group include an alkyl group having 1 to 6 carbon atoms such as anethyl group, a methyl group, an i-propyl group, a n-propyl group, as-butyl group, a t-butyl group, a pentyl group, a hexyl group, acyclopentyl group, a cyclohexyl group, etc., an alkoxy group having 1 to6 carbon atoms such as an ethoxy group, a methoxy group, an i-propoxygroup, a n-propoxy group, a s-butoxy group, a t-butoxy group, a pentoxygroup, a hexyloxy group, a cyclopentoxy group, a cyclohexyloxy group,etc., an aryl group having 5 to 40 ring atoms, an amino groupsubstituted with an aryl group having 5 to 40 ring atoms, an ester groupwhich has an aryl group having 5 to 40 ring atoms, an ester group whichhas an alkyl group having 1 to 6 carbon atoms, a cyano group, a nitrogroup, a halogen atom and the like. Ar⁵ includes preferably a naphthylgroup, an anthranyl group, a chrysenyl group, a pyrenyl group or an arylgroup represented by the general formula (D), of which each may besubstituted.

The following is a description of the construction of the organic ELdevice of the present invention.

Typical examples of the construction of the organic EL device of thepresent invention include:

-   (1) an anode/a light emitting layer/a cathode;-   (2) an anode/a hole injecting layer/a light emitting layer/a    cathode;-   (3) an anode/a light emitting layer/an electron injecting layer/a    cathode;-   (4) an anode/a hole injecting layer/a light emitting layer/an    electron injecting layer/a cathode;-   (5) an anode/an organic semiconductor layer/a light emitting layer/a    cathode;-   (6) an anode/an organic semiconductor layer/an electron barrier    layer/a light emitting layer/a cathode;-   (7) an anode/an organic semiconductor layer/a light emitting    layer/an adhesion improving layer/a cathode;-   (8) an anode/a hole injecting layer/a hole transporting layer/a    light emitting layer/an electron injecting layer/a cathode;-   (9) an anode/an insulating layer/a light emitting layer/an    insulating layer/a cathode;-   (10) an anode/an inorganic semiconductor layer/an insulating layer/a    light emitting layer/an insulating layer/a cathode;-   (11) an anode/an organic semiconductor layer/an insulating layer/a    light emitting layer/an insulating layer/a cathode;-   (12) an anode/an insulating layer/a hole injecting layer/a hole    transporting layer/a light emitting layer/an insulating layer/a    cathode; and-   (13) an anode/an insulating layer/a hole injecting layer/a hole    transporting layer/a light emitting layer/an electron injecting    layer/a cathode.    Among those, the construction (8) is generally employed in    particular; however, the construction of the organic EL device is    not limited to those shown above as the examples.

In general, the organic EL device is produced on a substrate whichtransmits light. It is preferable that the substrate which transmitslight has a transmittance of light of 50% or greater in the visibleregion of 400 to 700 nm. It is also preferable that a flat and smoothsubstrate is employed.

As the substrate which transmits light, for example, glass sheet andsynthetic resin sheet are advantageously employed. Specific examples ofthe glass sheet include soda ash glass, glass containing barium andstrontium, lead glass, aluminosilicate glass, borosilicate glass, bariumborosilicate glass, quartz and the like. In addition, specific examplesof the synthetic resin sheet include sheet made of polycarbonate resins,acrylic resins, polyethylene terephthalate resins, polyether sulfideresins, polysulfone resins and the like.

The anode in the organic EL device of the present invention covers arole of injecting holes into a hole transport layer or into a lightemitting layer, and it is effective that the anode has a work functionof 4.5 eV or greater. Specific examples of the material for the anodeinclude indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver,platinum, copper and the like.

With regard to the cathode, its material preferably has a small workfunction with the aim of injecting electrons into an electron transportlayer or into a light emitting layer. The anode can be prepared byforming a thin film of the electrode material described above inaccordance with a process such as a vapor deposition process or asputtering process. When the light emitted from the light emitting layeris observed through the anode, it is preferable that the anode has atransmittance of the emitted light greater than 10%. It is alsopreferable that the sheet resistivity of the anode is several hundredΩ/□ or smaller. The thickness of the anode is, in general, selected inthe range of from 10 nm to 1 μm and preferably in the range of from 10to 200 nm depending on a kind of the materials.

In the organic EL device of the present invention, the light emittinglayer has the following functions:

-   (1) The injecting function: the function of injecting holes from the    anode or the hole injecting layer and injecting electrons from the    cathode or the electron injecting layer when an electric field is    applied;-   (2) The transporting function: the function of transporting injected    charges (electrons and holes) by the force of the electric field;    and-   (3) The light emitting function: the function of providing the field    for recombination of electrons and holes and leading the    recombination to the emission of light.    As the process for forming the light emitting layer, a well known    process such as the vapor deposition process, the spin coating    process and the LB process can be employed.

It is preferable that a light emitting layer is a molecularsedimentation film particularly. Here, the molecular sedimentation filmis defined as a thin film formed by sedimentation of a gas phasematerial compound or a thin film formed by condensation of a liquidphase material compound. The molecular sedimentation film may bedifferentiated from a thin film (a molecular build-up film) formed bythe LB process, base on the differences between agglomeration structuresand higher-order structures, and also the differences resulting fromfunctionalities thereof. In addition, as shown in Japanese PatentLaid-open No. Showa57(1982)-51781, to form a light emitting layer, athin film may be formed in accordance with the spin coating and the likeof the solution to be prepared by dissolving a binder such as resin anda material compound in solvent.

In the present invention, any well known light emitting material otherthan a light emitting material consisting of an asymmetric pyrenederivative of the present invention may be optionally contained in thelight emitting layer; or a light emitting layer containing other wellknown light emitting layer may be laminated with the light emittinglayer containing the light emitting material of the present inventioneach in an extent of not obstructing to achieve the objective of thepresent invention respectively.

In the present invention, the hole injecting layer and the holetransporting layer are layers which assist injection of holes into thelight emitting layer and transport the holes to the light emitting zone.The layers exhibit a great mobility of holes and, in general, have anionization energy as small as 5.5 eV or smaller For the hole injectinglayer and the hole transporting layer, a material which transports holesto the light emitting layer at a small strength of the electric field ispreferable. A material which exhibits, for example, a mobility of holesof at least 10⁻⁴ cm²/V·sec under application of an electric field offrom 10⁴ to 10⁶ V/cm is preferable. As for such material, any arbitrarymaterial selected from conventional material commonly used as a chargetransporting material for the holes in photoconducting materials andwell known material employed for the hole injecting layer in the ELdevice is usable.

Further examples include triazole derivatives (refer to U.S. Pat. No.3,112,197, etc.), oxadiazole derivatives (refer to U.S. Pat. No.3,189,447, etc.), imidazole derivatives (refer to Japanese ExaminedPatent KOKOKU No. Shou 37-16096, etc.), poly arylalkane derivatives(refer to U.S. Pat. Nos. 3,615,402, 3,820,989 and 3,542,544, JapaneseExamined Patent KOKOKU Nos. Shou 45-555 and Shou 51-10983, JapaneseUnexamined Patent Application Laid-Open Nos. Shou 51-93224, Shou55-17105, Shou 56-4148, Shou 55-108667, Shou 55-156953, Shou 56-36656,etc.), pyrazoline derivatives and pyrazolone derivatives (refer to U.S.Pat. Nos. 3,180,729 and 4,278,746, Japanese Unexamined ApplicationPatent Laid-Open Nos. Shou 55-88064, Shou 55-88065, Shou 49-105537, Shou55-51086, Shou 56-80051, Shou 56-88141, Shou 57-45545, Shou 54-112637,Shou 55-74546, etc.), phenylenediamine derivatives (refer to U.S. Pat.No. 3,615,404, Japanese Examined Patent KOKOKU Nos. Shou 51-10105, Shou46-3712 and Shou 47-25336, Japanese Unexamined Patent ApplicationLaid-Open Nos. Shou 54-53435, Shou 54-110536, Shou 54-119925, etc.),arylamine derivatives (refer to U.S. Pat. Nos. 3,567,450, 3,180,703,3,240,597, 3,658,520, 4,232,103, 4,175,961 and 4,012,376, JapaneseExamined Patent KOKOKU Nos. Shou 49-35702 and Shou 39-27577, JapaneseUnexamined Patent Application Laid-Open Nos. Shou 55-144250, Shou56-119132 and Shou 56-22437, West German Patent No. 1,110,518, etc.),chalcone derivatives which is substituted with amino group (refer toU.S. Pat. No. 3,526,501, etc.), oxazole derivatives (disclosed in U.S.Pat. No. 3,257,203, etc.), styryl anthracene derivatives (refer toJapanese Unexamine Patent Application Laid-Open No. Shou 56-46234,etc.), fluorenone derivatives (refer to Japanese Unexamined PatentApplication Laid-Open No. Shou 54-110837, etc.), hydrazone derivatives(refer to U.S. Pat. No. 3,717,462, Japanese Unexamined PatentApplication Laid-Open Nos. Shou 54-59143, Shou 55-52063, Shou 55-52064,Shou 55-46760, Shou 55-85495, Shou 57-11350, Shou 57-148749, Hei2-311591, etc.), stilbene derivatives (refer to Japanese UnexaminedPatent Application Laid-Open Nos. Shou 61-210363, Shou 61-228451, Shou61-14642, Shou 61-72255, Shou 62-47646, Shou 62-36674, Shou 62-10652,Shou 62-30255, Shou 60-93455, Shou 60-94462, Shou 60-174749, Shou60-175052, etc.), silazane derivatives (U.S. Pat. No. 4,950,950),polysilane-based copolymers (Japanese Unexamined Patent ApplicationLaid-Open No. Hei 2-204996), aniline-based copolymers (JapaneseUnexamined Patent Application Laid-Open No. Hei 2-282263), anelectroconductive polymer oligomer which is disclosed in JapaneseUnexamined Patent Application Laid-Open No Hei 1-211399 (particularly,thiophene oligomer), etc.

With regard to the material of the hole injecting layer, the abovematerials are also employable, however, porphyrin compounds, aromatictertiary amine compounds and styryl amine compounds (refer to U.S. Pat.No. 4,127,412, Japanese Unexamined Patent Application Laid-Open Nos.Shou 53-27033, Shou 54-58445, Shou 54-149634, Shou 54-64299, Shou55-79450, Shou 55-144250, Shou 56-119132, Shou 61-295558, Shou 61-98353,Shou 63-295695, etc.) are preferable and the aromatic tertiary aminecompounds are particularly preferable. Further examples include, forexample, 4,4′-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (abbreviated asNPD hereunder) having 2 fused aromatic rings in its molecular describedin U.S. Pat. No. 5,061,569,4,4′,4″-tris(N-(3-methylphenyl)-N-phenylamino)triphenyl amine(abbreviated as MTDATA hereunder) made by connecting three triphenylamine units to form a star burst type, etc. Further, in addition to theaforementioned aromatic dimethylidene based compounds described as amaterial for the light emitting layer, an inorganic compound such asp-type silicon, p-type silicon carbide or so is employable as thematerial for the hole injecting layer.

To form the hole injecting layer or the hole transporting layer, a thinfilm may be formed from the material for the hole injecting layer or thehole transporting layer, respectively, in accordance with a well knownprocess such as the vacuum vapor deposition process, the spin coatingprocess, the casting process and the LB process. Although the thicknessof the hole injecting layer and the hole transporting layer is notparticularly limited, the thickness is usually from 5 nm to 5 μm. When ahole transportation zone comprises a compound of the present invention,the hole injecting/transporting layer may be constructed by a layerconsisting of at least one of the aforementioned materials, and also thehole injecting/transporting layer may be laminated by a holeinjecting/transporting layer consisting of a compound different fromthem.

In the organic EL device of the present invention, the organicsemiconductor layer assists to inject the holes or to inject theelectrons into the light emitting layer, and it is preferable for theorganic semiconductor layer to have a electric conductivity of 10⁻¹⁰S/cm or greater. With regard to a material for the organic semiconductorlayer, electroconductive oligomers such as an oligomer having thiophene,an oligomer having arylamine disclosed in Japanese Laid-Open No. Heisei8(1996)-193191 and so on, electroconductive dendrimers such as adendrimer having an arylamine and so on are employable.

The electron injection/transporting layer in the organic EL device ofthe present invention is a layer which assists injection of electronsinto the light emitting layer and exhibits a great mobility ofelectrons. Among the electron injecting layers, an adhesion improvinglayer is a layer made of a material exhibiting excellent adhesion withthe cathode. As the material for the electron injecting layer,8-hydroxyquinoline, metal complexes of derivatives thereof andoxadiazole derivatives are preferable. Examples of the8-hydroxyquinoline and metal complexes of derivatives thereof includemetal chelates of oxinoid compounds including chelates of oxine (ingeneral, 8-quinolinol or 8-hydroxyquinoline). For example,tris(8-quinolino)aluminum (Alq) can be employed as the electroninjecting material. Further, examples of the oxadiazole delivertivesinclude an electron transfer compound shown as the following generalformulae:

In the general formulae above Ar^(1′), Ar^(2′), Ar^(3′), Ar^(5′),Ar^(6′) and Ar^(9′) each independently represents a substituted orunsubstituted aryl group, which may be the same with or different fromeach other; Ar^(4′), Ar^(7′) and Ar^(8′) each independently represents asubstituted or unsubstituted arylene group, which may be the same withor different from each other. Examples of the aryl group include aphenyl group, a biphenyl group, an anthranil group, a perilenyl groupand a pyrenyl group. Further, examples of the arylene group include aphenylene group, a naphthylene group, a biphenylene group, ananthranylene group, a perilenylene group, the pyrenylene group and thelike. Furthermore, examples of the substituent include an alkyl grouphaving 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbonatoms, a cyano group and the like. With regard to the electron transfercompound, those compounds having a thin film forming capability arepreferable.

Specific examples of the electron transfer compounds are shown below:

In the present invention, it is preferable that a reductive dopant isadded in either the electron transporting zone or an interfacial zonebetween the cathode and the organic layer. The reductive dopant used inthe present invention is defined as a substance which reduces theelectron transporting compound. Examples of the reductive dopant includeat least one compound selected from alkali metals, alkali metalliccomplexes, alkali metal compounds, alkaline earth metals, alkaline earthmetallic complexes, alkaline earth metal compounds, rare earth metals,rare earth metallic complexes and rare earth metal compounds.

Examples of the preferable reductive dopant include at least one alkalimetal selected from a group consisting of Na (the work function: 2.36eV), K (the work function: 2.28 eV), Rb (the work function: 2.16 eV) andCs (the work function: 1.95 eV) or at least one alkaline earth metalsselected from a group consisting of Ca (the work function: 2.9 eV), Sr(the work function: 2.0 to 2.5 eV) and Ba (the work function: 2.52 eV);whose work function of 2.0 eV or less is particularly preferable. Amongthe above, the preferable reductive dopant include at least one alkalimetal selected from a group consisting of K, Rb and Cs, the morepreferred is Rb or Cs, and the most preferred is Cs. These alkali metalshave particularly high ability of reduction so that improvement of anemission luminance and longer lasting of a lifetime of the organic ELdevice may be realized. In addition, a combination of two or more ofalkali metals is also preferable as a reductive dopant having 2.9 eV orless of the work function. In particular, a combination of Cs, forexample with Na, K or Rb, or Na and K is preferable. By a combing andcontaining Cs therein, the reduction ability can be demonstratedeffectively, and improvement of an emission luminance and longer lastingof a lifetime of the organic EL device may be realized by adding it intoan electron injecting area.

In the organic EL device of the present invention, an electron injectinglayer formed with an insulating material or a semiconductor may befurther interposed between the cathode and the organic thin film layer.The electron injecting layer effectively prevents leak in the electriccurrent and improves the electron injecting capability. It is preferablethat at least one metal compound selected from the group consisting ofalkali metal chalcogenides, alkaline earth metal chalcogenides, alkalimetal halides and alkaline earth metal halides is used as the insulatingmaterial. It is preferable that the electron injecting layer isconstituted with the above alkali metal chalcogenides since the electroninjecting property can be improved. Preferable examples of the alkalimetal chalcogenides include Li₂O, LiO, Na₂S, Na₂Se and NaO. Preferableexamples of the alkaline earth metal chalcogenide s include CaO, BaO,SrO, BeO, BaS and CaSe.

Preferable examples of the alkali metal halides include LiF, NaF, KF,LiCl, KCl, NaCl and the like. Preferable examples of the alkaline earthmetal halides include fluorides such as CaF₂, BaF₂, SrF₂, MgF₂ and BeF₂and halides other than the fluorides.

Examples of the semiconductor constituting the electron transportinglayer include oxides, nitrides and oxide nitrides containing at leastone element selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg,Si, Ta, Sb and Zn, which are used singly or in combination of two ormore. It is preferable that the inorganic compound constituting theelectron transporting layer is in the form of a fine crystalline oramorphous insulating thin film. When the electron transporting layer isconstituted with the above insulating thin film, a more uniform thinfilm can be formed and defective pixels such as dark spots can bedecreased. Examples of the inorganic compound include the alkali metalchalcogenides, the alkaline earth metal chalcogenides, the alkali metalhalides and the alkaline earth metal halides which are described above.

As the cathode for the organic EL device of the present invention, anelectrode substance such as metal, alloy, electroconductive compound andthose mixture having a small work function (4 eV or smaller) isemployed. Examples of the electrode substance include potassium,sodium-potassium alloy, magnesium, lithium, magnesium-silver alloy,aluminum/aluminum oxide, Al/Li₂O, Al/LiO₂, Al/LiF, aluminum-lithiumalloy, indium, rare earth metal and the like. The cathode can beprepared by forming a thin film of the electrode material describedabove in accordance with a process such as the vapor deposition processand the sputtering process. When the light emitted from the lightemitting layer is observed through the cathode, it is preferable thatthe cathode has a transmittance of the emitted light greater than 10%.It is also preferable that the sheet resistivity of the cathode isseveral hundred Ω/□ or smaller. The thickness of the cathode is, ingeneral, selected in the range of from 10 nm to 1 μm and preferably inthe range of from 50 to 200 nm.

In general, an organic EL device tends to form defects in pixels due toleak and short circuit since an electric field is applied to ultra-thinfilms. To prevent the formation of the defects, a layer of an insulatingthin film may be inserted between the pair of electrodes. Examples ofthe material employed for the insulating layer include aluminum oxide,lithium fluoride, lithium oxide, cesium fluoride, cesium oxide,magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride,aluminum nitride, titanium oxide, silicon oxide, germanium oxide,silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide,vanadium oxide and the like. Mixtures and laminates of the abovecompounds can also be employed.

To produce an organic EL device of the present invention, for example, acathode, a light emitting layer and, where necessary, a hole injectinglayer and an electron injecting layer are formed in accordance with theaforementioned process using the aforementioned materials, and the anodeis formed in the last step. An organic EL device may be produced byforming the aforementioned layers in the order reverse to that describedabove, i.e., an anode being formed in the first step and a cathode inthe last step. An embodiment of the process for producing an organic ELdevice having a construction in which a cathode, a hole injecting layer,a light emitting layer, an electron injecting layer and an anode aredisposed sequentially on a light-transmitting substrate will bedescribed in the following. On a suitable light-transmitting substrate,a thin film made of a material for the cathode is formed in accordancewith the vapor deposition process or the sputtering process so that thethickness of the formed thin film is 1 μm or smaller and preferably inthe range of 10 to 200 nm. The formed thin film is employed as thecathode.

Then, a hole injecting layer is formed on the cathode. The holeinjecting layer can be formed in accordance with the vacuum vapordeposition process, the spin coating process, the casting process or theLB process, as described above. The vacuum vapor deposition process ispreferable since a uniform film can be easily obtained and thepossibility of formation of pin holes is small. When the hole injectinglayer is formed in accordance with the vacuum vapor deposition process,in general, it is preferable that the conditions in general are suitablyselected in the following ranges: temperature of the deposition source:50 to 450° C.; vacuum level: 10⁻⁷ to 10⁻³ Torr; deposition rate: 0.01 to50 nm/second; temperature of the substrate: −50 to 300° C.; and filmthickness: 5 nm to 5 μm; although the conditions of the vacuum vapordeposition are different depending on the employed compound (thematerial for the hole injecting layer) and the crystal structure and therecombination structure of the hole injecting layer to be formed.

Subsequently, the light-emitting layer is formed on the hole-injectinglayer formed above. Also the formation of the light emitting layer canbe made by forming the light emitting material according to the presentinvention into a thin film in accordance with the vacuum vapordeposition process, the sputtering process, the spin coating process orthe casting process. The vacuum vapor deposition process is preferablebecause a uniform film can be easily obtained and the possibility offormation of pinholes is small. When the light-emitting layer is formedin accordance with the vacuum vapor deposition process, in general, theconditions of the vacuum vapor deposition process can be selected in thesame ranges as those described for the vacuum vapor deposition of thehole-injecting layer although the conditions are different depending onthe used compound. It is preferable that the thickness is in the rangeof from 10 to 40 nm.

Next, the electron-injecting layer is formed on the light-emitting layerformed above. Similarly to the hole injecting layer and thelight-emitting layer, it is preferable that the electron-injecting layeris formed in accordance with the vacuum vapor deposition process since auniform film must be obtained. The conditions of the vacuum vapordeposition can be selected in the same ranges as those for the holeinjecting layer and the light-emitting layer.

In the last step, the anode is formed on the electron-injecting layer,and an organic EL device can be fabricated. The anode is made of a metaland can be formed in accordance with the vacuum vapor deposition processor the sputtering process. It is preferable that the vacuum vapordeposition process is employed in order to prevent the lower organiclayers from damages during the formation of the film.

In the above production of the organic EL device, it is preferable thatthe above layers from the anode to the cathode are formed successivelywhile the production system is kept in a vacuum after being evacuated.The process for forming the layers in the organic EL device of thepresent invention is not particularly limited. A conventional processsuch as the vacuum vapor deposition process and the spin coating processcan be used.

The organic thin film layer comprising the compound having a spiro bondrepresented by the foregoing general formula (1) used in the organic ELdevice of the present invention can be formed in accordance with thevacuum vapor deposition process, the molecular beam epitaxy process (theMBE process) or, using a solution prepared by dissolving the compoundinto a solvent, in accordance with a conventional coating process suchas the dipping process, the spin coating process, the casting process,the bar coating process and the roller coating process. The thickness ofeach layer in the organic thin film layer in the organic EL device ofthe present invention is not particularly limited, therefore, athickness within the range of several nanometers to 1 μm is preferableso as to reduce the defects such as pin holes and improve theefficiency.

When a direct voltage is applied on the organic EL device produced inthe above manner, when a direct voltage of 5 to 40 V is applied in thecondition that the cathode is connected to a positive electrode (+) andthe anode is connected to a negative electrode (−), then a lightemitting is observed. When the connection is reversed, no electriccurrent is produced and no light is emitted at all. When an alternatingvoltage is applied on the organic EL device, the uniform light emissionis observed only in the condition that the polarity of the cathode ispositive and the polarity of the anode is negative. When an alternatingvoltage is applied on the organic EL device, any type of wave shape canbe employed.

EXAMPLE

This invention will be described in further detail with reference toExamples, which does not limit the scope of this invention.

Synthesis Example 1 Synthesis of 1-bromo-4-phenylnaphthalene

15 g of 1,4-dibromonaphthalene on the market, 7.7 g of phenylboronicacid and 1.8 g of tetrakis(triphenylphophine)palladium were mixed,followed by argon displacement. After adding 200 ml of toluene and 90 mlof 2M sodium carbonate aqueous solution thereto, it was refluxed onheating for 7 hours. After standing to cool, the organic layer wasextracted by toluene, and then it was washed by water and saturated saltwater. Subsequently the organic layer was dried by using sodium sulfateanhydride, and then the solvent was removed by distillation. The productwas refined through a silica gel chromatography and then 8.9 g of1-4-bromo-4-phenylnaphthalene of white crystal was obtained (Yield:60%).

Synthesis Example 2 Synthesis of 1-bromo-4-(naphthelene-2-yl)naphthalene

The procedure of Synthesis Example 1 was repeated except that2-naphthalene boronic acid in place of phenylboronic acid was used, andthen 7.5 g of 1-bromo-4-(naphthalene-2-yl)naphthalene of white crystalwas obtained (yield: 43%). Synthesis Example 3 (Synthesis of2-(biphenyl-2-yl)-6-bromonaphthelene) 15 g of 2,6-dibromonaphthalene onthe market, 12.5 g of 2-biphenylboronic acid and 1.8 g oftetrakis(triphenylphophine)palladium were mixed, followed by argondisplacement. After adding 250 ml of toluene and 90 ml of 2M sodiumcarbonate aqueous solution thereto, it was refluxed on heating for 7hours. After standing to cool, the organic layer was extracted bytoluene, and then it was washed by water and saturated salt water.Subsequently the organic layer was dried by using sodium sulfateanhydride, and then the solvent was removed by distillation. The productwas refined through a silica gel chromatography and then 10.9 g of2-(biphenyl-2-yl)-6-bromonaphthalene of white crystal was obtained(yield: 58%).

Synthesis Example 4 Synthesis of 9-(naphthalene-2-yl)anthracene

22.5 g of 9-bromoanthracene, 15.8 g of 2-naphthelene boronic acid and2.0 g of tetrakis(triphenylphophine)palladium were mixed, followed byargon displacement. After adding 150 ml of toluene and 140 ml of 2Msodiumcarbonate aqueous solution thereto, it was refluxed on heating for7 hours. After standing to cool, the crystal precipitated was filtratedit was washed by ethanol and toluene. The crystal obtained wasrecrystallized in toluene, followed by filtering and drying, and then23.1 g of 9-(naphthalene-2-yl)anthracene was obtained (yield: 87%).

Synthesis Example 5 Synthesis of 9-bromo-10-(naphthalene-2-yl)anthracene

23.1 g of 9-(naphthalene-2-yl)anthracene was dispersed into 250 ml ofDMF (dimethylformamide), and then 14.9 g of NBS (N-bromosuccinimide) inDMF solution (150 ml) was dropped therein. After stirred at roomtemperature for 7 hours, it was left over a night. 200 ml of water wasadded thereto, and then the crystal precipitated was separated byfiltration. Subsequently it was washed by ethanol adequately, followedby drying, and 28.8 g of 9-bromo-10-(naphthalene-2-yl)anthracene ofbeige color crystal was obtained (Yield: 99%).

Synthesis Example 6 Synthesis of10-(naphthalene-2-yl)anthracene-9-boronic acid

Under argon atmosphere, 150 ml of dehydrated toluene and 150 ml ofdehydrated ether were added to 28.8 g of9-bromo-10-(naphthalene-2-yl)anthracene, and it was cooled to −63 deg C.58 ml of 1.58M-n-butyllithium/hexane solution was dropped therein.Subsequently, it was stirred at −63 deg C. for 30 minutes, followed byheating up to −10 deg C. It was cooled to −70 deg C. again, and 23.4 mlof trimethyl boronic acid ester/dehydrated ether solution was droppedtherein stepwise. After it was stirred at −70 deg C. for 2 hours, it washeated to room temperature steadily. After left over a night, it wasacidified by 10% hydrochloric aqueous solution, followed by two timeextractions by toluene. The organic layer obtained was washed bysaturated salt water and then dried by using sodium sulfate anhydride.After the solvent was removed by distillation, the crystal obtained wasrecrystallized in toluene/hexane, followed by drying, and then 17 g of10-(naphthalene-2-yl)anthracene-9-boronic acid was obtained (yield:65%).

Synthesis Example 7 Synthesis of 9-phenanthrene boronic acid

80 ml of dehydrated toluene and 160 ml of dehydrated THF(tetrahydrofuran) were added to 38.6 g of 9-bromophenanthrene, and wascooled to −40 deg C. After 106 ml of 1.58M n-butyllithium hexanesolution was dropped, it was stirred at −40 deg C. for 30 minutes andheated to −10 deg C. It was cooled to −70 deg C. again, and 50.0 ml oftrimethyl boronic acid ester/dehydrated ether solution was droppedtherein stepwise. Subsequently, it was stirred at −70 deg C. for 2 hoursand then heated to room temperature steadily. After left over a night,it was acidified by 10% hydrochloric aqueous solution, followed by twotime extractions by toluene. The organic layer obtained was washed bysaturated salt water and then dried by using sodium sulfate anhydride.After the solvent was removed by distillation, the crystal obtained wasrecrystallized in toluene/hexane, followed by drying, and then 21.5 g of9-phenanthrene boronic acid of pale brown color crystal was obtained(yield: 64%).

Synthesis Example 8 Synthesis of10-(phenanthrene-9-yl)anthracene-9-boronic acid

The procedures of Synthesis Example 4 to 6 were repeated, except that9-phenanthrene boronic acid in place of 2-naphthalene boronic acid asthe starting material was used, and then10-(phenanthrene-9-yl)anthracene-9-boronic acid was obtained.

Production Example 1 Synthesis of AN7

5.0 g of 1-bromo-4-phenylnaphthalene, 7.38 g of10-(naphthalene-2-yl)anthracene-9-boronic acid and 0.61 g oftetrakis(triphenylphophine)palladium were mixed, and followed by argondisplacement. After adding 100 ml of DME (dimethoxyethane) and 30 ml of2M sodium carbonate aqueous solution thereto, it was refluxed on heatingfor 10 hours.

After standing to cool, the crystal precipitated was filtrated, it waswashed by water, methanol and then toluene. The crystal obtained wasrecrystallized in toluene, followed by filtering and drying, and then6.37 g of AN7 of cream color crystal was obtained (yield: 71%).

The measurement result of the compound by FD-MS (Field Desorption MassSpectrometry analysis) showed m/z (measured value)=506 to C₄₀H₂₆=506,therefore the objective compound (AN7) was confirmed.

Production Example 2 Synthesis of AN8

The procedure of Production Example 1 was repeated except that1-bromo-4-(naphthalene-2-yl)naphthalene in place of1-bromo-4-phenylnaphthelene was used, and then AN8 of cream colorcrystal was obtained (yield: 63%).

The measurement result of the compound by FD-MS showed m/z=556 toC₄₄H₂₈=556, therefore the objective compound (AN8) was confirmed.

Production Example 3 Synthesis of AN11

The procedure of Production Example 1 was repeated, except that2-bromonaphthalene and 10-(phenanthrene-9-yl)anthracene-9-boronic acidin place of 1-bromo-4-phenylnaphthelene and10-(naphthalene-2-yl)anthracene-9-boronic acid respectively were used,and then AN11 of cream color crystal was obtained (yield: 67%).

The measurement result of the compound by FD-MS showed m/z=480 toC₃₈H₂₄=480.

Production Example 4 Synthesis of AN13

The procedure of Production Example 1 was repeated except that2-(biphenyl-2-yl)-6-bromonaphthalene and10-(phenanthrene-9-yl)anthracene-9-boronic acid in place of1-bromo-4-phenylnaphthelene and10-(naphthalene-2-yl)anthracene-9-boronic acid respectively were used,and then AN13 of cream color crystal was obtained (yield: 67%).

The measurement result of the compound by FD-MS showed m/z=632 toC₅₀H₃₂=632.

Production Example 5 Synthesis of AN44

The procedure of Production Example 1 was repeated except that1-bromonaphthelene in place of 1-bromo-4-naphthalene was used, and thenAN44 of cream color crystal was obtained (yield: 69%).

The measurement result of the compound by FD-MS showed m/z=430 toC₃₄H₂₂=430.

Production Example 6 Synthesis of AN6

The procedure of Production Example 1 was repeated except that2-bromo-6-phenylnaphthelene in place of 1-bromo-4-naphthalene was used,and then AN6 of cream color crystal was obtained (yield: 54%).

The measurement result of the compound by FD-MS showed m/z=506 toC₄₀H₂₆=506.

Production Example 7 Synthesis of AN12

The procedure of Production Example 1 was repeated except that2-bromo-6-phenylnaphthelene and10-(phenanthrene-9-yl)anthracene-9-boronic acid in place of1-bromo-4-naphthalene and 10-(naphthalene-2-yl)anthracene-9-boronic acidrespectively were used, and then AN13 of cream color crystal wasobtained (yield: 60%).

The measurement result of the compound by FD-MS showed m/z=556 toC₄₄H₂₈=556.

Example 1 Fabrication of an Organic EL Device

A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1mm thickness having an ITO transparent electrode was cleaned byapplication of ultrasonic wave in isopropyl alcohol for 5 minutes andthen by exposure to ozone generated by ultraviolet light for 30 minutes.The cleaned glass substrate having an ITO transparent electrode line wasfixed to a substrate holder of a vacuum deposition apparatus, and on thesurface, where the ITO transparent electrode line was fixed, of thesubstrate, a film (hereinafter referred to as TPD232 film) having filmthickness of 60 nm of the followingN,N′-bis(N,N′-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4′-diamino-1,1′-biphenylwas formed so as to cover the transparent electrode. The TPD232 filmperforms as a hole injecting layer.

Subsequently, a layer having layer thickness of 20 nm of the followingN,N,N′,N′-tetra(4-biphenyl)-diaminobiphenylene was formed (hereinafterreferred to as TBDB layer). The layer performs as a hole transportinglayer.

Subsequently, a film having a film thickness of 40 nm of theaforementioned compound AN-7 was formed as a hole transporting layer bya vapor deposition. Concurrently, as a light emitting material, thefollowing amino compound D1 containing a styryl group was deposited atthe ratio by weight between AN7 and D1 of 40:3 by a vapor deposition.The film performs as a light emitting layer. On the film, a film havinga Alq film thickness of 10 nm was formed. The film performs as anelectron injecting layer.

Further, a film (film thickness: 10 nm) of Alq:Li (the source oflithium: manufactured by SAES GETTERS Company) as an electron injectinglayer or a cathode was formed by binary vapor deposition of Li as areductive dopant and the following Alq. On the Alq:Li film, Al metal wasdeposited to form a metal cathode; therefore, an organic EL device wasfabricated.

The current efficiency of the organic EL device was measured, and alsothe half lifetime thereof was measured at an initial luminance of 1,000nits. The results are shown in Table 1.

Examples 2 to 7 Fabrication of Organic EL Devices

Organic EL devices were fabricated similar to the example 1 except thatthe compounds described in Table 1 were used in place of the compoundAN7, and then the current efficiencies and half lifetimes of the devicesobtained were tested by the similar method to Example 1. The results areshown in Table 1.

Examples 8 Fabrication of Organic EL Device

Organic EL device was fabricated similar to the example 1 except thatthe compound AN11 in place of the compound AN7 and the amine compound D2in place of the amine compound D1 were used as the material for thelight emitting layer, and then the current efficiency and half lifetimeof the device obtained were tested by the similar method to Example 1.The results are shown in Table 1.

Comparative Example 1

Organic EL devices were fabricated similar to the example 1 except thatan1 as used in place of the compound AN7, and then the currentefficiency and half lifetime of the device obtained was tested by thesimilar methods to Example 1.

The results are shown in Table 1.

TABLE 1

an1 Compound of Current Half Light-Emitting Efficiency Lifetime Layer(cd/A) (hours) Example 1  AN7/D1 10.9 4,200 Example 2  AN8/D1 10.8 4,200Example 3 AN11/D1 11.0 5,800 Example 4 AN13/D1 10.8 3,700 Example 5AN44/D1 10.0 3,000 Example 6  AN6/D1 10.1 3,300 Example 7 AN12/D1 10.84,900 Example 8 AN11/D2 10.3 3,700 Comparative an-/D1 9.0 2,200 Example1

As shown in Table 1, the organic EL devices of Examples 1 to 8 exhibiteda higher current efficiency and a longer lifetime than those of thedevice of Comparative Example 1.

What we claim is:
 1. A light emitting material for an organicelectroluminescent device comprising an asymmetric anthracene derivativerepresented by formula (1):

wherein, A¹ represents a 1-naphthyl group; A² represents a 1-naphthylgroup or a 2-naphthyl group; Ar¹ represents a hydrogen atom; Ar²represents a hydrogen atom, a substituted or unsubstituted aromatichydrocarbon ring group having ring carbon atoms of 6 to 50; R¹ to R⁸each independently represents a hydrogen atom, a substituted orunsubstituted aromatic hydrocarbon ring group having ring carbon atomsof 6 to 50, a substituted or unsubstituted aromatic hetero ring grouphaving ring atoms of 5 to 50, a substituted or unsubstituted alkyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstitutedcycloalkyl group having carbon atoms of 3 to 50, a substituted orunsubstituted alkoxy group having carbon atoms of 1 to 50, a substitutedor unsubstituted aralkyl group having carbon atoms of 6 to 50, asubstituted or unsubstituted aryloxy group having carbon atoms of 5 to50, a substituted or unsubstituted arylthio group having carbon atoms of5 to 50, a substituted or unsubstituted alkoxycarbonyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted silyl group, acarboxyl group, a halogen atom, a cyano group, a nitro group or ahydroxyl group; R⁹ represents a hydrogen atom; R¹⁰ represents a hydrogenatom, a substituted or unsubstituted aromatic hydrocarbon ring grouphaving ring carbon atoms of 6 to 50, a substituted or unsubstitutedalkyl group having carbon atoms of 1 to 50, a substituted orunsubstituted cycloalkyl group having carbon atoms of 3 to 50, asubstituted or unsubstituted aralkyl group having carbon atoms of 6 to50, a substituted or unsubstituted aryloxy group having carbon atoms of5 to 50, a substituted or unsubstituted arylthio group having carbonatoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstituted silylgroup, a carboxyl group, a halogen atom, a cyano group, a nitro group ora hydroxyl group, and none of R⁹ and R¹⁰ is alkenyl group; Ar² and R¹⁰each are optionally a plural number, and two neighboring groups thereofoptionally form a saturated or unsaturated ring structure; wherein thesubstituent groups at the 9^(th) and 10^(th) positions of the anthraceneat the core in formula (1) are different from each other; and whereinthe light emitting material is located in a light emitting layer of anorganic electroluminescence device.
 2. The light emitting material forthe organic electroluminescent device according to claim 1, wherein, informula (1), Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group,9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthrylgroup, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group and 4″-t-butyl-p-terphenyl-4-yl group.3. The light emitting material for the organic electroluminescent deviceaccording to claim 1, wherein, in formula (1), Ar² represents any one ofa hydrogen atom, phenyl group, 1-naphthyl group, 2-naphthyl group, and9-phenanthryl group.
 4. An organic electroluminescent device comprisingat least one organic thin film layer, which comprises at least a lightemitting layer, which interposed between a pair of electrode comprisingan anode and a cathode, wherein a light emitting zone comprises thelight emitting material for the organic electroluminescent deviceaccording to claim 1 singly or as a component of a mixture thereof. 5.The organic electroluminescent device according to claim 4, wherein, theorganic thin film layer comprises the light emitting material for theorganic electroluminescent device.
 6. The organic electroluminescentdevice according to claim 4, wherein, the light emitting layer furthercomprises an arylamine compound.
 7. The organic electroluminescentdevice according to claim 4, wherein, the light emitting layer furthercomprises a styrylamine compound.
 8. The organic electroluminescentdevice according to claim 4, wherein, the light emitting layer comprisesthe light emitting material for the organic electroluminescent devicesingly or as a component of a mixture thereof.
 9. The light emittingmaterial for the organic electroluminescent device according to claim 1,wherein, in formula (1), R¹⁰ represents any one of a hydrogen atom,phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group,methyl group, ethyl group, propyl group, isopropyl group, n-butyl group,s-butyl group, isobutyl group and t-butyl group.
 10. The light emittingmaterial for the organic electroluminescent device according to claim 1,wherein, in formula (1), R¹ to R⁸ each independently represents any oneof a hydrogen atom, phenyl group, 1-naphthyl group, 2-naphthyl group,9-phenanthryl group, methyl group, ethyl group, propyl group, isopropylgroup, n-butyl group, s-butyl group, isobutyl group and t-butyl group.11. The light emitting material for the organic electroluminescentdevice according to claim 1, wherein, in formula (1), Ar¹ represents ahydrogen atom, Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group and 2-naphthyl group, R⁹ represents a hydrogen atom,R¹⁰ represents any one of a hydrogen atom, phenyl group, 1-naphthylgroup and 2-naphthyl group, R¹ to R⁸ each independently represents anyone of a hydrogen atom, phenyl group, methyl group and t-butyl group.12. The light emitting material for the organic electroluminescentdevice according to claim 1, wherein, in formula (1), Ar¹ represents ahydrogen atom, Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group and 2-naphthyl group, R⁹ represents a hydrogen atom,R¹⁰ represents a hydrogen atom, R¹ to R⁸ each represents a hydrogenatom.
 13. The light emitting material for the organic electroluminescentdevice according to claim 1, wherein, in formula (1), Ar¹ represents ahydrogen atom, Ar² represents any one of phenyl group, 1-naphthyl groupand 2-naphthyl group R⁹ represents a hydrogen atom; R¹⁰ represents ahydrogen atom, R¹ to R⁸ each represents a hydrogen atom.
 14. A lightemitting material for an organic electroluminescent device comprising anasymmetric anthracene derivative selected from the compounds AN6, AN9,AN10, AN11, AN12, AN13, AN14, AN15, AN16, AN23, AN24, AN28, AN29, AN31,AN38, AN40, AN41, AN42, AN45, and AN46:


15. An organic electroluminescent device comprising at least one organicthin film layer, which comprises at least a light emitting layer, whichinterposed between a pair of electrode comprising an anode and acathode, wherein a light emitting zone comprises the light emittingmaterial for the organic electroluminescent device according to claim 14singly or as a component of a mixture thereof.
 16. The organicelectroluminescent device according to claim 15, wherein, the lightemitting layer comprises the light emitting material for the organicelectroluminescent device singly or as a component of a mixture thereof.17. The organic electroluminescent device according to claim 15,wherein, the organic thin film layer comprises the light emittingmaterial for the organic electroluminescent device.
 18. The organicelectroluminescent device according to claim 15, wherein, the lightemitting layer further comprises an arylamine compound.
 19. The organicelectroluminescent device according to claim 15, wherein, the lightemitting layer further comprises a styrylamine compound.
 20. An organicelectroluminescent device comprising at least one organic thin filmlayer between an anode and a cathode, wherein: the at least one organicthin film layer comprises a light emitting layer; the light emittinglayer comprises a host material; and the host material is selected froman asymmetric anthracene derivative represented by formula (1)

wherein, A¹ represents a 1-naphthyl group; A² represents a 1-naphthylgroup or a 2-naphthyl group; Ar¹ represents a hydrogen atom; Ar² eachindependently represents a hydrogen atom, a substituted or unsubstitutedaromatic hydrocarbon ring group having ring carbon atoms of 6 to 50; R¹to R⁸ each independently represents a hydrogen atom, a substituted orunsubstituted aromatic hydrocarbon ring group having ring carbon atomsof 6 to 50, a substituted or unsubstituted aromatic hetero ring grouphaving ring atoms of 5 to 50, a substituted or unsubstituted alkyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstitutedcycloalkyl group having carbon atoms of 3 to 50, a substituted orunsubstituted alkoxy group having carbon atoms of 1 to 50, a substitutedor unsubstituted aralkyl group having carbon atoms of 6 to 50, asubstituted or unsubstituted aryloxy group having carbon atoms of 5 to50, a substituted or unsubstituted arylthio group having carbon atoms of5 to 50, a substituted or unsubstituted alkoxycarbonyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted silyl group, acarboxyl group, a halogen atom, a cyano group, a nitro group or ahydroxyl group; R⁹ represents a hydrogen atom; R¹⁰ represents a hydrogenatom, a substituted or unsubstituted aromatic hydrocarbon ring grouphaving ring carbon atoms of 6 to 50, a substituted or unsubstitutedalkyl group having carbon atoms of 1 to 50, a substituted orunsubstituted cycloalkyl group having carbon atoms of 3 to 50, asubstituted or unsubstituted aralkyl group having carbon atoms of 6 to50, a substituted or unsubstituted aryloxy group having carbon atoms of5 to 50, a substituted or unsubstituted arylthio group having carbonatoms of 5 to 50, a substituted or unsubstituted alkoxycarbonyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstituted silylgroup, a carboxyl group, a halogen atom, a cyano group, a nitro group ora hydroxyl group, and none of R⁹ and R¹⁰ is alkenyl group; Ar² and R¹⁰each are optionally a plural number, and two neighboring groups thereofoptionally form a saturated or unsaturated ring structure; wherein thesubstituent groups at the 9^(th) and 10^(th) positions of the anthraceneat the core in formula (1) are different from each other.
 21. Theorganic electroluminescent device according to claim 20, wherein informula (1), Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group,9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthrylgroup, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl) phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group and 4″-t-butyl-p-terphenyl-4-yl group.22. The organic electroluminescent device according to claim 20, whereinin formula (1), Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group, 2-naphthyl group, and 9-phenanthryl group.
 23. Theorganic electroluminescent device according to claim 20, wherein informula (1), R¹⁰ represents any one of a hydrogen atom, phenyl group,1-naphthyl group, 2-naphthyl group, 9-phenanthryl group, methyl group,ethyl group, propyl group, isopropyl group, n-butyl group, s-butylgroup, isobutyl group and t-butyl group.
 24. The organicelectroluminescent device according to claim 20, wherein in formula (1),R¹ to R⁸ each independently represents any one of a hydrogen atom,phenyl group, 1-naphthyl group, 2-naphthyl group, 9-phenanthryl group,methyl group, ethyl group, propyl group, isopropyl group, n-butyl group,s-butyl group, isobutyl group and t-butyl group.
 25. The organicelectroluminescent device according to claim 20, wherein in formula (1),Ar¹ represents a hydrogen atom, Ar² represents any one of a hydrogenatom, phenyl group, 1-naphthyl group and 2-naphthyl group, R⁹ representsa hydrogen atom, R¹⁰ represents any one of a hydrogen atom, phenylgroup, 1-naphthyl group and 2-naphthyl group, R¹ to R⁸ eachindependently represents any one of a hydrogen atom, phenyl group,methyl group and t-butyl group.
 26. The organic electroluminescentdevice according to claim 20, wherein in formula (1), Ar¹ represents ahydrogen atom, Ar² represents any one of a hydrogen atom, phenyl group,1-naphthyl group and 2-naphthyl group, R⁹ represents a hydrogen atom,R¹⁰ represents a hydrogen atom, R¹ to R⁸ each represents a hydrogenatom.
 27. The organic electroluminescent device according to claim 20,wherein, the light emitting layer further comprises an arylaminecompound.
 28. The organic electroluminescent device according to claim20, wherein, the light emitting layer further comprises a styrylaminecompound.
 29. A light emitting material for an organicelectroluminescent device comprising an asymmetric anthracene derivativerepresented by formula (1):

wherein, A¹ represents a 1-naphthyl group; A² represents a 1-naphthylgroup or a 2-naphthyl group; Ar¹ represents a hydrogen atom; Ar²represents a substituted or unsubstituted aromatic hydrocarbon ringgroup having ring carbon atoms of 6 to 50; R¹ to R⁸ each independentlyrepresents a hydrogen atom, a substituted or unsubstituted aromatichydrocarbon ring group having ring carbon atoms of 6 to 50, asubstituted or unsubstituted aromatic hetero ring group having ringatoms of 5 to 50, a substituted or unsubstituted alkyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted cycloalkyl grouphaving carbon atoms of 3 to 50, a substituted or unsubstituted alkoxygroup having carbon atoms of 1 to 50, a substituted or unsubstitutedaralkyl group having carbon atoms of 6 to 50, a substituted orunsubstituted aryloxy group having carbon atoms of 5 to 50, asubstituted or unsubstituted arylthio group having carbon atoms of 5 to50, a substituted or unsubstituted alkoxycarbonyl group having carbonatoms of 1 to 50, a substituted or unsubstituted silyl group, a carboxylgroup, a halogen atom, a cyano group, a nitro group or a hydroxyl group;R⁹ represents a hydrogen atom; R¹⁰ represents a hydrogen atom, asubstituted or unsubstituted aromatic hydrocarbon ring group having ringcarbon atoms of 6 to 50, a substituted or unsubstituted alkyl grouphaving carbon atoms of 1 to 50, a substituted or unsubstitutedcycloalkyl group having carbon atoms of 3 to 50, a substituted orunsubstituted alkoxy group having carbon atoms of 1 to 50, a substitutedor unsubstituted aralkyl group having carbon atoms of 6 to 50, asubstituted or unsubstituted aryloxy group having carbon atoms of 5 to50, a substituted or unsubstituted arylthio group having carbon atoms of5 to 50, a substituted or unsubstituted alkoxycarbonyl group havingcarbon atoms of 1 to 50, a substituted or unsubstituted silyl group, acarboxyl group, a halogen atom, a cyano group, a nitro group or ahydroxyl group, and none of R⁹ and R¹⁰ is alkenyl group; Ar² and R¹⁰each are optionally a plural number, and two neighboring groups thereofoptionally form a saturated or unsaturated ring structure; wherein thesubstituent groups at the 9^(th) and 10^(th) positions of the anthraceneat the core in formula (1) are different from each other; and whereinthe light emitting material is located in a light emitting layer of anorganic electroluminescence device.
 30. The light emitting material forthe organic electroluminescent device according to claim 29, wherein, informula (1), Ar² represents any one of phenyl group, 1-naphthyl group,2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group,1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group and 4″-t-butyl-p-terphenyl-4-yl group.31. The light emitting material for the organic electroluminescentdevice according to claim 29, wherein, in formula (1), Ar² representsany one of phenyl group, 1-naphthyl group, 2-naphthyl group and9-phenanthryl group.
 32. The light emitting material for the organicelectroluminescent device according to claim 29, wherein, in formula(1), R¹ represents any one of a hydrogen atom, phenyl group, 1-naphthylgroup, 2-naphthyl group and 9-phenanthryl group, methyl group, ethylgroup, propyl group, isopropyl group, n-butyl group, s-butyl group,isobutyl group and t-butyl group.
 33. The light emitting material forthe organic electroluminescent device according to claim 29, wherein, informula (1), R¹ to R⁸ each independently represents any one of ahydrogen atom, phenyl group, 1-naphthyl group, 2-naphthyl group and9-phenanthryl group, methyl group, ethyl group, propyl group, isopropylgroup, n-butyl group, s-butyl group, isobutyl group and t-butyl group.34. The light emitting material for the organic electroluminescentdevice according to claim 29, wherein, in formula (1), Ar¹ represents ahydrogen atom, Ar² represents any one of phenyl group, 1-naphthyl groupand 2-naphthyl group R⁹ represents a hydrogen atom; R¹⁰ represents anyone of a hydrogen atom, phenyl group, 1-naphthyl group and 2-naphthylgroup, R¹ to R⁸ each independently represents any one of a hydrogenatom, phenyl group, methyl group and t-butyl group.